Triethylamine → (S)-N-(1-(5-bromo-2-(methylamino)pyrimidin-4-yl)-2-(3,5-difluorophenyl)ethyl)-2-(3-(difluoromethyl)-4,4,7,7-tetrafluoro-4,5,6,7-tetrahydro-1H-indazol-1-yl)acetamide

HRID 2170333Notes

Reaction equation

HRID 2170333 reaction equation
[Br:1][C:2]1[C:3]([C@@H:12]([NH:22][C:23](=[O:41])[CH2:24][N:25]2[C:33]3[C:32]([F:35])([F:34])[CH2:31][CH2:30][C:29]([F:37])([F:36])[C:28]=3[C:27]([CH:38]([F:40])[F:39])=[N:26]2)[CH2:13][C:14]2[CH:19]=[C:18]([F:20])[CH:17]=[C:16]([F:21])[CH:15]=2)=[N:4][C:5](S(C)(=O)=O)=[N:6][CH:7]=1.Cl.CN.[CH2:45]([N:47](CC)CC)C>ClCCl>[Br:1][C:2]1[C:3]([C@@H:12]([NH:22][C:23](=[O:41])[CH2:24][N:25]2[C:33]3[C:32]([F:35])([F:34])[CH2:31][CH2:30][C:29]([F:37])([F:36])[C:28]=3[C:27]([CH:38]([F:40])[F:39])=[N:26]2)[CH2:13][C:14]2[CH:19]=[C:18]([F:20])[CH:17]=[C:16]([F:21])[CH:15]=2)=[N:4][C:5]([NH:47][CH3:45])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 6364545Methylamine hydrochlorideHCID 90281385(S)-N-(1-(5-bromo-2-(methylsulfonyl)pyrimidin-4-yl)-2-(3,5-difluorophenyl)ethyl)-2-(3-(difluoromethyl)-4,4,7,7-tetrafluoro-4,5,6,7-tetrahydro-1H-indazol-1-yl)acetamide

Product 1

HCID 90281536(S)-N-(1-(5-bromo-2-(methylamino)pyrimidin-4-yl)-2-(3,5-difluorophenyl)ethyl)-2-(3-(difluoromethyl)-4,4,7,7-tetrafluoro-4,5,6,7-tetrahydro-1H-indazol-1-yl)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the mixture of compound 12C (68 mg, 0.1 mmol) and methylamine hydrochloride (34 mg, 0.5 mmol) in dichloromethane (5 ml) was added triethylamine (697 μL, 0.5 mmol). The reaction mixture was stirring at ambient temperature for 2 hours. The solvent was evaporated and the crude product was purified on reverse phase HPLC eluting with acetonitrile and water (with 0.1% TFA) to afford the title product. MS (m/z) 627.24 [M+H]+.

Workup

  1. customThe solvent was evaporated
  2. customthe crude product was purified on reverse phase HPLC
  3. washeluting with acetonitrile and water (with 0.1% TFA)

Sources & evidence

ORD record
ord-23965a81b118492da7b073022a47815c
Source dataset
uspto-grants-2015_06
Patent number
US09050344B2

Reaction notes

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